952511-48-7|5-Bromo-4-methyl-1H-benzo[d]imidazole| Ambeed

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Quality Control of [ 952511-48-7 ] Purity: 97% SDS Specification

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Product Details of [ 952511-48-7 ]

CAS No. :	952511-48-7
Formula :	C₈H₇BrN₂
M.W :	211.06
SMILES Code :	CC1=C2C(NC=N2)=CC=C1Br
MDL No. :	MFCD18642426
InChI Key :	JNXOUOKRAGYUNE-UHFFFAOYSA-N
Pubchem ID :	59214444

Safety of [ 952511-48-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 952511-48-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.12
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	48.76
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	28.68 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.52
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.54
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.63
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.06
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.15
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.38

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.35
Solubility	0.0934 mg/ml ; 0.000442 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.79
Solubility	0.343 mg/ml ; 0.00162 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.16
Solubility	0.0147 mg/ml ; 0.0000697 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.78 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.48

Application In Synthesis of [ 952511-48-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 952511-48-7 ]

[ 952511-48-7 ] Synthesis Path-Downstream 1~16

1
[ 122-51-0 ]
[ 290353-57-0 ]
[ 952511-48-7 ]

Yield	Reaction Conditions	Operation in experiment
73%		To a stirred solution of 1-bromo-2-methyl-3,4-dinitro-benzene (Tetrahedron Lett. 2000, 41(22), 4277-4279) (2.61 g, 10 mmol) in EtOH (50 mL) was added SnCl2 (1.89 g, 100 mmol). The mixture was stirred at 50° C. for 2 h. The mixture was cooled to rt, and triethylorthoformate (25 mL) was added. After heating for 30 min at 70° C., the mixture was cooled to rt, diluted with satd. aq. NaHCO3 (100 mL), and extracted with EtOAc (3.x.60 mL). The combined organic layers were washed with satd. aq. NaCl (100 mL), dried, and concentrated to give a solid residue. The residue was stirred vigorously with MeOH (100 mL) and the precipitate removed by filtration. The filtrate was concentrated to yield the crude product which was then purified by FCC (EtOAc/hexanes) to give 1.55 g (73percent) of the desired product. MS: mass calcd. for C8H7BrN2, 209.98; m/z found, 211.0 [M+H]+. 1H NMR (CD3OD): 8.18 (s, 1H), 7.41 (d, J=8.7 Hz, 1H), 7.34 (d, J=8.6 Hz, 1H), 2.61 (s, 3H).

References: [1]Patent: US2009/156613,2009,A1 .Location in patent: Page/Page column 22.

2
[ 64-18-6 ]
[ 952511-74-9 ]
[ 952511-48-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogenchloride; water; at 60℃; for 12h;	3: A mixture of 156 (28 g,140 mmol), formic acid (240 mL) and 37percent> concentrated HC1 (400 mL) was heated to 60 °C for 12 h, cooled in an ice-water bath, and the pH slowly adjusted to 8-9 with 28percent> concentrated NH4OH. The solid was collected by filtration, washed with water and dried in air to afford 25 g (98percent) of 5-bromo-4-methyl-lH-benzo[d]imidazole (158) as a yellow solid: MS (ESI) m/z = 213 [M+l]+.
		4-Bromo-3-methyl-1,2-benzenediamine (6.89 g, 34.3 mmol), formic acid (60 ml) and 37percent concentrated HCl (150 ml) were heated at 60° C. for 12 h, cooled in an ice-water bath, and slowly adjusted with 28percent concentrated ammonium solution (280 ml) to pH8-9. The solid was collected by filtration, washed with water and dried in air to afford the title compound as a pinkish white solid.1H NMR (400 MHz, DMSO-d6) delta ppm 2.58 (s, 3H) 7.32 (s, 2H) 8.20 (s, 1H) 12.62 (br., 1H); (M+1) 212.94, 1.11 min (LC/MS method A)

References: [1]Patent: WO2013/26914,2013,A1 .Location in patent: Page/Page column 143.
[2]Patent: US2010/222345,2010,A1 .Location in patent: Page/Page column 87.

3
[ 952511-48-7 ]
[ 76-83-5 ]
[ 1008361-60-1 ]

Yield	Reaction Conditions	Operation in experiment
		<strong>[952511-48-7]5-Bromo-4-methyl-1H-benzimidazole</strong> (6.62 g, 31.36 mmol) was dissolved in anhydrous tetrahydrofuran (150 ml) and cooled to 0° C. Sodium hydride oil dispersion (60percent, 1.55 g, 38.75 mmol) was slowly added. The mixture was stirred for 1 h at 0° C. Triphenylmethyl chloride and a catalytic amount of tetrabutylammonium iodide were added. The resultant mixture was heated at reflux for 12 h, cooled to room temperature, quenched with saturated ammonium chloride solution (50 ml) and partitioned between ethyl acetate and water. The organic phase was separated, washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was suspended in 50 ml of 50percent ethyl acetate in hexanes, heated to reflux, cooled to room temperature and filtered to afford the title compound as a pale brown solid. The filtrate was concentrated and purified by silica gel column chromatography (5 to 20percent ethyl acetate in hexanes) to give more title compound.1H NMR (400 MHz, CDCl3) delta ppm 2.70 (s, 3H) 6.19 (d, 1H) 7.00-7.20 (m, 7H) 7.20-7.45 (m, 9H) 7.92 (s, 1H); LC-MS: (Ph3C+) 243.11, 3.27 min (LC/MS method A)

References: [1]Patent: US2010/222345,2010,A1 .Location in patent: Page/Page column 87.

4
[ 110-87-2 ]
[ 952511-48-7 ]
[ 1425933-54-5 ]

Yield	Reaction Conditions	Operation in experiment
57%	With toluene-4-sulfonic acid; In tetrahydrofuran; at 80℃;	Example 46N4-(5-Cyclopropyl- 1 H-pyrazol-3-yl)-N2-methyl-N2-((4-methyl- 1 H-b enzo [d] imidazol-5- yl)methyl)pyrimidine-2,4-diamine (1-95)step 1 : To a solution of 5-bromo-4-methyl-lH-benzo[d]imidazole (1.0 g, 4.74 mmol, CASRN 952511-48- 7) and 3,4-dihydro-2H-pyran (2.0 g, 23.70 mmol) in THF (10 mL) was added / TsOH-H20 (90 mg, 0.47 mmol). The mixture was heated at 80 °C overnight, cooled and the solvent was removed in vacuo. The residue was diluted with DCM (100 mL) and water (50 mL). The organic layer was separated, dried (MgSO i), filtered and concentrated to dryness in vacuo. The crude product was purified by Si02 chromatography eluting with a petroleum ether/EtOAc gradient (10 to 50percent EtOAc) to afford 800 mg (57percent) of 5-bromo-4-methyl-l -(tetrahydro- 2H-pyran-2-yl)-lH-benzo[d]imidazole (254) as light yellow solid: MS (ESI) m/z = 295.1 [M+l]+.

References: [1]Patent: WO2013/26914,2013,A1 .Location in patent: Page/Page column 162; 163.

5
zinc cyanide [ No CAS ]
[ 952511-48-7 ]
[ 952511-70-5 ]

Yield	Reaction Conditions	Operation in experiment
53%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; zinc; In N,N-dimethyl-formamide; at 120℃; for 2h;Inert atmosphere;	step 4: A mixture of 158 (21 g; 99 mmol), Zn(CN)2 (23.2 g; 198 mmol), Pd(dppf)Cl2 (6.4 g; 9.9 mmol) and zinc (258 mg; 4 mmol) in dry DMF (150 mL) under inert atmosphere was heated at 120 °C for 2 h. The reaction mixture was filtered through a pad of Celite® that was washed with EtOAc. The organics were washed with water, dried (MgSO i), filtered and evaporated in vacuo. The crude product was purified by Si02 chromatography eluted with a DCM/MeOH gradient (0 to 10percent> MeOH) to afford 8.3 g (53percent>) of 4-methyl-lH-benzo[d]imidazole-5-carbonitrile (160) as a brown solid: MS (ESI) m/z = 158 [M+l]+.

References: [1]Patent: WO2013/26914,2013,A1 .Location in patent: Page/Page column 143.

6
[ 55289-35-5 ]
[ 952511-48-7 ]

References: [1]Patent: WO2013/26914,2013,A1 .
[2]Biochemical and Biophysical Research Communications,2015,vol. 456,p. 282 - 287.

7
[ 290353-57-0 ]
[ 952511-48-7 ]